Today and tomorrow, Grierson & Leitch honors America by spotlighting films that exemplify the best our country has to offer—and the worst. Today: Movies that made us feel worse about America.

Tim Grierson: Dogville

For all the charges of anti-Americanism leveled at Danish director Lars von Trier's Dogville, it's impossible to watch the film and think that somebody who hates the United States made it. To spend a three-hour drama agonizing over the hypocrisy and moral failings of a tiny Rocky Mountain community during the Depression, you can't hate America—you've got to be obsessed with and fascinated by and deeply, deeply conflicted about the country, viewing it more as a concept than as an actual place.

Dogville is set on a mostly bare stage with chalk outlines to represent the different homes and buildings. A Brechtian twist on Our Town, the film's production design more closely resembles a play than a movie, von Trier's attempt to make his story universal but also unsettlingly disconnected from reality. Dogville stars Nicole Kidman as Grace, a helpless innocent on the run from gangsters, and the town's residents—led by idealistic young writer Tom (Paul Bettany)—embrace the chance to prove that their community is filled with the spirit of charity and hospitality, allowing her to live with them for a trial period before holding a vote to see if she can stay permanently. Of course, it's little surprise that Dogville's story ends up playing out far, far differently than Tom's utopian aspirations would have imagined, but Grace's slow descent into a living hell ends up being a tart critique of how even the noblest of intentions can be undone by faulty groupthink and fear of outsiders.

Whether it's Do the Right Thing or Magic Mike, there have been plenty of films that dramatize all the ways that human beings can ruin their paradises, but von Trier's is probably the most upsetting and bracing. And that's because it comes from a person that, deep down, really wants America to be Ronald Reagan's shining city on the hill. Von Trier's relationship with America (which he's never visited because of a fear of flying) is almost that of a jilted, betrayed lover—he can't believe what she's done to herself. If he didn't care so much, he wouldn't bother.

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It's important to remember that Dogville premiered at the Cannes Film Festival in May 2003, two months after the U.S. had invaded Iraq and thus squandered the sympathy and goodwill we'd built up around the world after 9/11. Our Middle Eastern adventure came with its own set of hypocrisies and utopian aspirations, and there were echoes of it in the way that the residents of Dogville professed their high moral standing while systematically destroying Grace. The film turned out to be weirdly prescient in the most unfortunate of ways.

In Dogville, Von Trier isn't above resorting to cheap shots to egg on his audience—the satiric use of "Young Americans" over the end credits is way too cute—but the film at its core is reminding all of us (Americans or not) that there is nothing more dangerous in the world than a group of people who are absolutely convinced of their own righteousness. Dogville doesn't hate America, but it does expect us as a superpower to set a good example for the planet. In an election year, that's not the worst request to keep in mind.

Will Leitch: Roger & Me

There was a time—and I swear this is true—that Michael Moore wasn't the gasbag that he is now, a media manipulator more interested in his own cause than those that he champions. Or at least didn't seem to be. (Moore is one of those guys who you find yourself feeling guilty about agreeing with.) Back in 1988, Moore was just an alt-weekly editor in Michigan who was appalled by what had happened to his hometown of Flint, Mich., in the wake of General Motors' decision to close plants there and move those jobs to Mexico. The devastation wrought on Flint by the plant closings inspired Moore's one-man quest to find GM CEO Roger Smith and demand an explanation.

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But "demand" is such a strong word, such a 2000s-era Moore word to describe what goes on in Roger & Me. What Moore does in the film is more of a "shamble"; it's sort of amazing, watching the film today, just how appealing a screen presence he really is. He feels like an everyman regular fella, genuinely befuddled that Smith is so difficult to track down, deeply saddened by what has happened to his beloved hometown. He's also not so ideologically tunnel-visioned that he doesn't slow down every once in a while and revel in some of the goofiness that surrounds him, from the infamous "Pets or Meat" lady or the guy who has probably given too much at the blood bank. ("The Flint Plasma Center is open on Mondays and Tuesdays and Wednesdays and Thursdays and Fridays. Saturdays and Sunday, they're closed." Moore has a satirist's eye in Roger & Me, more than an activist's one. At the time there were comparisons to Mark Twain. That sounds idiotic now and probably should have then; basically, "both of them are funny and from the Midwest." But the spirit was there: This was a film that used comedy to shed light on something tragic and horrible.

But then again, does it seem all that tragic and horrible anymore? The reason Roger & Me affected me even more this weekend than it did when I saw it more than 20 years ago is because so little of it seems outrageous now. A massive corporation closing down American factories because labor is cheaper elsewhere? Yawn, you say: This has been official American policy over the past five, even six presidential administrations now. Looking at the film today, the movie's faith and trust in the implicit power of unions is quaint and adorable, like watching an old movie in which the whole plot could be resolved by two cellphone calls in the first five minutes; now, unions are so weak that no one—not even many liberals—remembers what a difference they made in the first place. The world that Moore documents in Roger & Me is sad and cold and bereft. In the last 20 years, it has gotten so, so much worse.

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I think that's why Roger & Me still resonates, in a way that's even larger than it did initially. Its laments are heartbreakingly passé; its pessimism now feels like optimism. There weren't any other movies made about CEOs and boards of directors shutting down American factories after this one because it became so common no one even questioned it anymore. (We now just call it painfully obvious good business.) The outrages of that film aren't outrageous anymore; they're just the way business is done. The Roger Smiths of the world won. Many people praised Roger & Me as an example of film's ability to inspire change. But I have to say: Looking at it now, I'm pretty sure that's the exact opposite of what happened. Frankly, the only thing that's changed since that movie is the guy who directed it.

Grierson & Leitch is a regular column about the movies. Follow us on Twitter, @griersonleitch.